The Pseudocalanolides: Structure Revision of Calanolides C and D

Nmr spectra of synthetic structures corresponding to those initially reported for natural compounds calanolide C [1] and calanolide D [2] showed some subtle differences from those of the natural products. Further analysis has resulted in revision of the structures of the natural compounds, now renam...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1995-06, Vol.58 (6), p.916-920
Main Authors: McKee, Tawnya C, Cardellina, John H, Dreyer, Geoffrey B, Boyd, Michael R
Format: Article
Language:English
Subjects:
AIDS/HIV
CALOPHYLLUM
CALOPHYLLUM INOPHYLLUM
calophyllum lanigerum var. austrocoriaceum
CHEMICAL COMPOSITION
CHEMISTRY
CHIMIE
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
COUMARINE
COUMARINS
Coumarins - chemistry
Coumarins - pharmacology
CUMARINAS
DERIVATIVES
GUTTIFERAE
HIV Reverse Transcriptase
HIV-1 - enzymology
Leucine Zippers
Magnetic Resonance Spectroscopy
MOLECULAR CONFORMATION
molecular structure
Plants, Medicinal - chemistry
QUIMICA
Reverse Transcriptase Inhibitors
STEREOCHEMISTRY
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Summary:Nmr spectra of synthetic structures corresponding to those initially reported for natural compounds calanolide C [1] and calanolide D [2] showed some subtle differences from those of the natural products. Further analysis has resulted in revision of the structures of the natural compounds, now renamed pseudocalanolides C [3] and D [4]. The absolute stereochemistry of pseudocalanolide C was established as [6S, 7S, 8R] using the modified Mosher's method.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50120a015